Methyl-2-hydroxyalkyl sulfoxides



United States Patent 3,491,154 METHYL-Z-HYDROXYALKYL SULFOXIDES Hill M. Priestley, North Bergen, and James H. Wilson, Demarest, N.J., assignors to Lever Brothers Company,

New York, N.Y., a corporation of Maine No Drawing. Continuation-impart of application Ser. No. 365,487, May 6, 1964. This application Sept. 7, 1966, Ser. No. 577,603

Int. Cl. C07c 147/14 U.S. Cl. 260-607 1 Claim ABSTRACT OF THE DISCLOSURE Methyl-B-hydroxydodecyl sulfoxide useful as a detergent and foam stabilizer.

The present invention relates to novel methyl-Z-hydroxyalkyl sulfoxides which are useful as detergents and foam stabilizers.

This application is a continuation-in-part of our copending application, Ser. No. 365,487, filed May 6, 1964, which in turn was a continuation-in-part of our applications, Ser. Nos. 725,505, filed Apr. 1, 1958, and 60,546, filed Oct. 5, 1960, all now abandoned.

Alkyl sulfoxides having a long chain fatty acid residue are known to have surface active properties. U.S. Patent No. 2,787,595 to Webb discloses the use of alkyl sulfoxides as the essential active ingredient in detergent compositions. According to Webb, th sulfoxides may be employed per se as the essential active ingredient in detergent compositions, but preferably are employed in combination with inorganic builder salts. It is also stated in the patent that other synthetic detergents may be employed as detergency supplements in combination with the sulfoxides and that foam stabilizers may be added.

In accordance with the present invention, novel compounds are provided having the following formula:

wherein R is a hydroxyalkyl radical having from 8 to 18 carbon atoms. The methyl-Z-hydroxyalkyl sulfoxides are preferred, and a preferred species of this group of compounds is methyl-Z-hydroxydodecyl sulfoxide,

C H CHOHCH SOCH These compounds are also known as methyl-B-hydroxyalkyl sulfoxides.

It has been found that the presence of small amounts of the sulfoxides of this invention improves the stability of the foam produced by agitating aqueous solutions of suds-producing materials selected from the group consisting of anionic, ampholytic and nonionic organic synthetic detergents. The preferred methyl-Z-hydroxydodecyl sulfoxide is exceptionally stable in the presence of household bleach.

The term suds-producing materials selected from the group consisting anionic, ampholytic and nonionic organic synthetic detergents, as employed herein, is intended to include those anionic, ampholytic and nonionic compounds which are commonly employed as the essen tial active ingredient of suds-producing detergent compositions.

Suitable anionic suds-producing organic synthetic detergents include the alkyl aryl sulfonates, such as sodium dodecyl benzene sulfonate or ammonium pentadecyl benzene sulfonate, and the methyl taurates, such as Igepon TK-32, a sodium N-methyl-N- tall oil acid taurate, and Igepon TE-42, an N-methyl acyl taurate derived Patented Jan. 20, 1970 from tallow. Also included are the sulfated fatty alcohols, such as sodium lauryl sulfate and ammonium lauryl alcohol sulfate; the sulfated polyethylene oxide esters of resins or fatty acids, such as the ammonium salt of sulfated nonyl phenol condensed with four moles of ethylene oxide; and Sipon LT-6, a triethanolamine lauryl alcohol sulfate.

Suitable nonionic suds-producing organic synthetic detergents which may be employed according to this invention include Oronite NI-8589, a dodecyl phenol condensed with more than 10, i.e., 20 to 30 moles of ethylene oxide; Triton X-100, an alkyl aryl polyether alcohol, i.e., octylphenol condensed with 10 moles of ethylene oxide; Tergitol NP-l4, an alkyl phenol polyethylene glycol ether; Neutronyx 600, an aromatic polyglycol either condensate; Stereox A], a tridecyl alcohol condensed with 10 moles of ethylene oxide; and Sterox CD, a tall oil condensed with 10 moles of ethylene oxide.

Also suitable are Deriphat No. 154, a tallow disodiurn betaimino dipropionate, and sodium cocoglycinate. These are ampholytic substances.

Conventional soaps and inorganic builder salts, such as the phosphates, silicates, sulfates and the like, are not included within the term suds-producing materials selected from the group consisting of anionic, ampholytic and nonionic organic synthetic detergents used herein, although these materials can be used as auxiliary agents in the compositions of this invention. Also excluded from this class are the sulfoxides described above. The benefits of this invention are not obtained by merely increasing the concentration of the sulfoxide of this invention in the detergent composition.

The methyl-Z-hydroxyalkyl sulfoxides of the present invention are effective at varying levels depending upon the particular organic synthetic detergent used and upon the nature of the specific sulfoxide employed. Generally speaking, the sulfoxides are effective as suds stabilizers at levels above about 0.1% in detergent compositions containing operable levels of suds-producing organic synthetic detergents.

A general type of reaction which may be employed in preparing the sulfoxides is described in detail in U.S. Patent No. 2,787,595.

The following example illustrates a method of preparing suitably pure sulfoxides for use according to the present invention.

EXAMPLE 1 A C -hydroxyIated sulfoxide, specifically 2-hydroxydodecyl methyl sulfoxide, was prepared by treating dodecylene chlorohydrin, C H CHOHCH CI with methyl mercaptan in sodium ethylene solution. The sulfide thus formed was oxidized with nitric acid to the hydroxylated sulfoxide, C H CHOHCH SOCH This compound was useful as a suds stabilizing additive to a suds-producing organic synthetic detergent system; it was stable in the presence of household bleach.

EXAMPLE 2 Ingredient: Percent Dodecyl benzene sulfonic acid active) 7.0 Sodium xylene sulfonate (37% active) 18.9 Sodium silicate (37.5% solids) 7.0 Potassium hydroxide 2.4

A C-IZ-hydroxylated methyl sulfoxide,

C H CHOHCH SOCH 3.5 Laurie isopropanol amide 1.7 Tetrapotassium pyrophosphate 19.1 Water and miscellaneous ingredients 40.4

Example 2 represents a heavy duty liquid detergent prepared with the sulfoxide of this invention. These materials are exceptionally useful in dish washing and in heavy duty laundering. The example uses a combination of lauric isopropanol amide and a C-12-hydroxylated methyl sulfoxide as the foam stabilizing additive. The resulting detergent composition produces an exceptionally stable foam in aqueous solution and provides the required action in the presence of a bleaching agent.

EXAMPLE 3 The methyl-2-hydroxydodecyl sulfoxide prepared according to Example 1, was incorporated in a spray dried detergent composition to provide a detergent powder having the following composition:

Percent Na phenyltetrapropyleuesulfonate 18.00 Methyl-Z-hydroxydodecyl sulfoxide 3.50 Sodium toluenesulfonate 2.00 Sodium silicate solids (SiO :Na O=2.0) 6.00 Sodium tripolyphosphate 15.00 Tetrasodium pyrophosphate 25.00 Sodium carboxymethyl cellulose 0.50 Sodium sulfate 20.95 Misc. inert matter .Q.. 2.00

, Percent Optical brighteners and antitarnish agent 0.05 Water 7.00

References Cited UNITED STATES PATENTS 2,859,248 11/1958 Louthan 260607 3,247,258 4/ 1966 Anderson 260-607 CHARLES B. PARKER, Primary Examiner D. R. PHILLIPS, Assistant Examiner US. Cl. X.R. 252-94, 161 

